Friedman is my first choice simply because I think what he is doing is harder than what Theo did. Go write him a very very large check.

I have mad respect for Friedman too but to disregard “what Theo did” as not as impressive as Friedman is not, in my opinion, taking a hard look at what he’s built and how he’s done it.

The Red Sox minor league system has been a veritable gold mine for awhile now, and of the current productive core in place, only Adrian Gonzalez and Beckett didn’t come up through the system (and they were purchased with the system). That leaves Pedroia, Youkilis, Ellsbury, Lester, Papelbon, Bard, Buchholz. That’s a pretty goddamned good yield, and without the benefit of an endless stream of number one picks either.

As far as free agent signings go…yeah Theo’s hit and missed. But that’s every GM with dollars to spend. And to be fair here, most of the moves Theo made were lauded at the time (and many of them worked out too), including the current millstone being hung around his neck, John Lackey, who was a 4 WAR pitcher before he signed with Boston, was paid like a 4 WAR pitcher, and, in his first year, produced a 4 WAR season. That he cracked up this year and pitched like utter dogshit (as bad as he was, he still put up 1.5 WAR) wasn’t something anybody thought would happen as fast as it did. But hey, shit happens.

And as mb astutely pointed out, who is to say Friedman would fare any better with a bigger payroll? It’s not a guarantee that he would just because he’s done so well with a small one (this is the guy who, with pocket change to spend on the free agent market, thought Pat Burrell and the remains of Manny Ramirez would be good ideas, so it’s not just a string of number one hits here). Additionally, there are other unknowns with Friedman, including the ability to handle the pressure of a big market, and especially one like Chicago. Not one of the seven fans who go to Tampa games could pick Friedman out of a lineup even if he was wearing a big sign that said “hey you assholes, I’m Andrew Fucking Friedman” while in Boston, those crazy motherfuckers can pick Theo out of a crowd while wearing a gorilla suit on Halloween. There’s no such thing as “media pressure” in St. Petersburg. Do they even have a fucking newspaper outside of the Del Boca Vista Breeze?

Whereas Theo’s thrived in one of the most stressful sports environments there is, with a lynch mob for a fan base and an ownership group and team president who, to put it mildly, like to meddle. This is not to take anything away from Friedman, an excellent GM who has found quite a bit of success the past few years in spite of his own set of difficult circumstances (and if he ends up being the guy, count me on board), but Theo’s a fucking rock star, the PR home run, the guy you go after first.